Dimethylamine → (4-Dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester

HRID 32847ノート

反応式

HRID 32847 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][NH:18][CH3:19].O1CCCC1>S(Cl)(Cl)=O.CO>[CH3:17][N:18]([CH3:19])[C:14]([C:12]1[N:13]=[C:9]([NH2:8])[S:10][CH:11]=1)=[O:16].[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:16])[N:18]([CH3:19])[CH3:17])[N:13]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 15020512-Amino-1,3-thiazole-4-carboxylic acid, N-BOC protected

生成物 2

HCID 545942972-amino-N,N-dimethyl-1,3-thiazole-4-carboxamideHCID 86603401(4-Dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester収率 48%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 24386Thionyl Chloride溶媒

反応条件

温度
80 °C

実験手順

2-Amino-thiazole-4-carboxylic acid dimethylamide was prepared as follows. (1) A solution of 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid (0.5 g, 2 mmol) (prepared as described in Examples 4a and 4b) in thionyl chloride (10 mL) was heated at reflux (80° C.) for 2 hours. The reaction mixture was then concentrated under reduced pressure. To the residue was added a 2 M solution of dimethylamine in tetrahydrofuran (10 mL, 20 mmol) and methanol (10 mL). The reaction mixture was stirred at room temperature for 20 hours and concentrated. The residue was purified by chromatography over silica gel eluted with 2:1 ethyl acetate/hexanes to give (4-dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester as a yellow foam (0.26 g, 48%).

後処理

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography over silica gel
  4. washeluted with 2:1 ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-fee1464fa8e24b5288cdc61705cefdd9
出典データセット
uspto-grants-2008_09
特許番号
US07427635B2

反応ノート

読み込み中…